(6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol

• ChemBase ID: 131124
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• SMILES: CCCCCc1cc(c2c(c1)OC([C@H]1[C@H]2C=C(CC1)CO)(C)C)O
• Canonical SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2C=C(CO)CC1)(C)C
• InChI: InChI=1S/C21H30O3/c1-4-5-6-7-14-11-18(23)20-16-10-15(13-22)8-9-17(16)21(2,3)24-19(20)12-14/h10-12,16-17,22-23H,4-9,13H2,1-3H3/t16-,17-/m1/s1
• InChIKey: YCBKSSAWEUDACY-IAGOWNOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
• IUPAC Traditional name: (6aR,10aR)-9-(hydroxymethyl)-6,6-dimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromen-1-ol
• Synonyms: 7-Hydroxy-Δ1-tetrahydrocannabinol; 11-Hydroxy-Δ9-tetrahydrocannabinol; (6aR,10aR)-6a,7,8,10a-Tetrahydro-1-hydroxy-6,6-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-9-methanol; (-)-11-Hydroxy-9-THC; (-)-7-Hydroxy-1-tetrahydrocannabinol; 11-Hydroxy-Δ9-tetrahydrocannabinol; 11-Hydroxytetrahydrocannabinol; (-)-11-Δ9-Tetrahydro Cannabinol-9-methanol; 11-羟基-Δ9-四氢大麻酚

Database IDs

• CAS Number: 36557-05-8
• MDL Number: MFCD00151766
• PubChem SID: 162225402
• PubChem CID: 644022

CALCULATED PROPERTIES

• Acid pKa: 9.342414
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.663324
• LogD (pH = 7.4): 4.6584864
• Log P: 4.663386
• Molar Refractivity: 98.5082 cm^3
• Polarizability: 38.074955 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White to Pale Yellow Solid; vacuum-dried powder
• Melting Point: 136-138°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: HP6910000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-22
• Safety Statements: 36-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H361
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Drug Control: USDEA Schedule I; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - H5019

Application
用于鉴定 THC 代谢物的标准品

Toronto Research Chemicals - T293225

A metabolite of Δ9-Tetrahydrocannabinol (Δ9-THC) (T293200).

REFERENCES

• Manno, J., et al.: J. Anal. Toxicol., 25, 538 (2001)
• Skopp, G., et al.: Clin. Chem., 48, 301 (2001)
• Nadulski, T., et al.: Ther. Drug Monit., 27, 799 (2001)
• Blake, D., et al.: Rheumatology, 45, 50 (2001)